The paper reviews an assessment regime for its capacity to engage university learners, enabling them to design radically new business offerings. We explore the effect of the briefing approach on defining the customer/offering match. This study is framed by participatory action research, where data draws on two distinctive module deliveries: one where the design brief asks learners to generate the offering first and then shape the customer segment. The second one supplies an archetype and asks learners to define customer first and then develop the offering. Our analysis reveals that learners’ engagement with the design brief prompts an emergence of five patterns of learners’ responses, leading to conclusions that the nature of design brief elements has an impact in shaping the overall learning. Moreover, going from customer to offering appears to generate better iterations between the two, overall leading to learners’ engagement with the process not simply seeking an outcome.